Toluene → HCID 20627102, compound

HRID 2122050Notes

Reaction equation

HRID 2122050 reaction equation
[CH3:1][O:2][C:3]([C:5]1[NH:9][C:8]([C:10](=O)[CH2:11][CH2:12][C:13]([C:15]2[NH:16][C:17]([C:20]([O:22][CH3:23])=[O:21])=[CH:18][CH:19]=2)=O)=[CH:7][CH:6]=1)=[O:4].C1(C)C=CC=CC=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:41])=CC=1>CCOC(C)=O>[CH3:1][O:2][C:3]([C:5]1[NH:9][C:8]([C:10]2[S:41][C:13]([C:15]3[NH:16][C:17]([C:20]([O:22][CH3:23])=[O:21])=[CH:18][CH:19]=3)=[CH:12][CH:11]=2)=[CH:7][CH:6]=1)=[O:4]

Participants

5

Reactant 3

HCID 1140TolueneHCID 87949Lawesson's reagentHCID 20627101HCID 20627101, compound

Product 1

HCID 20627102HCID 20627102, compoundYield 70.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of compound 4 (1.73 g, 5.2 mmol), dry toluene (75 mL), and Lawesson's reagent (1.50 g, 3.7 mmol) was refluxed under an argon atmosphere for 12 hours. The solution was cooled to room temperature and concentrated to one-third its original volume in vacuo. Methanol was added slowly to the toluene until a precipitate appeared. Column chromatography was performed using pure CH2Cl2 (silica gel; 230-400 mesh) as the initial eluant to remove impurities. Conversion to a 50:50 hexanes:EtOAc eluant system yielded 0.86 g (2.6 mmol, 50%) of a yellow solid. 1H-NMR (CDCl3): δ 7.70 (s, 1H), 6.96 (dd, 1H), 6.52 (dd, 1H), 3.93 (s, 3H). 13C-NMR: δ 161.8, 134.0, 132.4, 125.7, 124.0, 117.8, 109.2, 52.2.

Workup

  1. temperaturewas refluxed under an argon atmosphere for 12 hours
  2. concentrationconcentrated to one-third its original volume in vacuo
  3. additionMethanol was added slowly to the toluene until a precipitate
  4. customto remove impurities

Sources & evidence

ORD record
ord-58b56ee46ac146349dcc01f958a88234
Source dataset
uspto-grants-2004_02
Patent number
US06696575B2

Reaction notes

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